Miyazawa et al. (U.S. Pat. No. 6,784,312) discloses polymerizable monomers represented by the general formulaCH2═C(R1)CO2—R2—[C(CF3)2OR3]n,wherein R1 is a hydrogen atom, a halogen atom, a hydrocarbon group or a fluorine-containing alkyl group; R2 is a straight-chain or branched alkyl group, a cyclic alkyl group, an aromatic group, or a substituent having at least two of these groups, the R2 being optionally partially fluorinated; R3 is a hydrogen atom, a hydrocarbon group that is optionally branched, a fluorine-containing alkyl group, or a cyclic group having an aromatic or alicyclic structure, the R3 optionally containing a bond of an oxygen atom or carbonyl group; and n is an integer of 1-2. Methods for synthesizing such monomers are also disclosed.
HFIBO (hexafluorobutylene oxide) is known to undergo ring-opening reactions with a variety of species to give fluoroalcohol-substituted products which range from 1/1 adducts to substituted HFIBO oligomers. (V. Petrov, Synthesis 2002, 2225; see also U.S. Pat. No. 6,653,419).
Nevertheless, there remains a need for a commercially viable synthetic route to certain fluoroalcohol-substituted (meth)acrylates that can be used to prepare fluoroalcohol-substituted polymers.